Sulfuric Acid → 8-Benzyl-3-phenyl-8-aza-bicyclo[3.2.1]oct-2-ene

Participants

Reaction Conditions

Reaction Steps

8-Benzyl-3-phenyl-8-aza-bicyclo[3.2.1]octan-3-ol (0.1 g, 0.34 mmol) was dissolved in TFA (1 mL) and cooled to 0° C. Concentrated sulphuric acid (0.054 mL) was added and the mixture stirred for 1 hour, then triethylsilane (0.17 mL) was added. After 2 hours the mixture was allowed to warm to room temperature, and then to stand for 60 hours. The mixture was concentrated under vacuum and diluted with a solution of saturated aqueous sodium carbonate. The products were extracted into DCM, dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum to give the title compound as a colourless oil. LCMS m/z 276.5 [M+H]+. R.T.=2.94 min (Analytical Method 4).

Provenance & Evidence